Polymorph- and molecular alignment-dependent lasing behaviors of a cyano-substituted thiophene/phenylene co-oligomer

Jinjyo, Tomomi; Mizuno, Hitoshi; Sasaki, Fumio; Yanagi, Hisao

doi:10.1039/d2tc04151k

Cited by 2 publications

(1 citation statement)

References 54 publications

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“…Among the variety of conjugated small molecules, symmetric aromatic hydrocarbon derivatives represent a convenient model for the fundamental study of "structure-property" relationships due to their condensed π-systems, known molecular packing extracted from X-ray data, low concentration of defects, and hence, outstanding charge carrier mobility and luminescent properties [5][6][7]. To tune a crystalline structure of organic semiconductors, several approaches were suggested and extensively exploited: variation of a conjugated framework [8][9][10][11], introduction of substituents [12][13][14][15][16][17], polymorphism [18][19][20][21][22][23], cocrystallization [24][25][26][27][28], template-induced [4,[29][30][31] and specific crystallizations [22,[32][33][34][35][36] allowing the control of crystal orientation on a substrate, and morphology. Polymorphism is considered to be one of the most powerful approaches in material science and pharmaceutical engineering for the study of "structure-activity" relationships and control of the properties of a given compound without changing its chemical structure [37][38][39].…”

Section: Introductionmentioning

confidence: 99%

Additive-Assisted Crystallization of 9,10-Diphenylanthracene

Sonina,

Cheshkina,

Kazantsev

2023

Crystals

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Crystallization control of organic conjugated small molecules is in high demand for the engineering of functional materials in organic optoelectronics. Here, we report solution additive-assisted crystallization of a model non-planar aromatic hydrocarbon derivative 9,10-diphenylanthracene. Among the studied series of related aromatic hydrocarbons comprising pyrene, perylene, anthracene, tetracene, and rubrene, only tetracene revealed clear reproducible effects allowing one to perform selective crystallization of metastable 9,10-diphenylanthracene polymorphs. Additionally, crystallization of 9,10-diphenylanthracene and pyrene produced a stoichiometric co-crystal (PYR–DPA) having a segregated layered molecular packing with alternating 9,10-diphenylanthracene and pyrene layers. Remarkably, the molecular packing of pyrene within the co-crystal is unique and represented by the herringbone motif, whereas the molecular packing in known pyrene polymorphs is represented by π-stacked molecules. The co-crystal also demonstrated a bright photoluminescence with a photoluminescence quantum yield of 51%. Considering the morphology of 9,10-diphenylanthracene crystals obtained and crystal structures of PYR–DPA co-crystal and tetracene, we have proposed the mechanism of additive-assisted polymorphism based on the inhibition of (111) facet of α-DPA and promoting of the layered structure crystallization corresponding to metastable polymorphs (β- and γ-DPA). We highlight the additive-assisted crystallization approach as a powerful tool for the crystal engineering of functional materials for organic optoelectronics.

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